3,4-dihydro-2H-pyran → Ethyl 2-[(oxan-2-yl)amino]-1,3-thiazole-5-carboxylate

HRID 1188123Notes

Reaction equation

HRID 1188123 reaction equation
[CH2:1]1[CH2:6][O:5][CH:4]=[CH:3][CH2:2]1.[NH2:7][C:8]1[S:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:12]=1>CC#N.C(O)(C(F)(F)F)=O>[O:5]1[CH2:6][CH2:1][CH2:2][CH2:3][CH:4]1[NH:7][C:8]1[S:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:12]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 3146282-Amino-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 43811197Ethyl 2-[(oxan-2-yl)amino]-1,3-thiazole-5-carboxylateYield 64%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6342AcetonitrileSolvent

Procedure

TFA (22 μL, 0.3 mmol) and DHP (3.9 mL, 43.5 mmol) were added to a suspension of ethyl 2-aminothiazole-5-carboxylate (5 g, 29 mmol) in CH3CN (40 mL) at RT. The resulting mixture was stirred at reflux overnight. The reaction mixture was concentrated and dissolved in AcOEt/PE and kept at 4 C overnight. The resultant white solid was filtrated and washed with PE, yielding ethyl 2-(tetrahydro-2H-pyran-2-ylamino)thiazole-5-carboxylate (4.73 g, 64%).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in AcOEt/PE
  4. customkept at 4 C overnight
  5. filtrationThe resultant white solid was filtrated
  6. washwashed with PE

Sources & evidence

ORD record
ord-a65753d0f76d484a97dbebe2223cb352
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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